N′-(2,4-Dichloro­benzyl­idene)-2-hydr­oxy-3-methyl­benzohydrazide

You-Yue Han; Qiu-Rong Zhao

doi:10.1107/S1600536810012419

. 2010 Apr 10;66(Pt 5):o1048. doi: 10.1107/S1600536810012419

N′-(2,4-Dichlorobenzylidene)-2-hydroxy-3-methylbenzohydrazide

You-Yue Han ^a,^*, Qiu-Rong Zhao ^a

PMCID: PMC2979063 PMID: 21579108

Abstract

In the title compound, C₁₅H₁₂Cl₂N₂O₂, the dihedral angle between the two benzene rings is 6.3 (2)°. The molecule adopts an E configuration with respect to the C=N bond. An intramolecular O—H⋯O hydrogen bond is observed. In the crystal structure, the molecules are linked through intermolecular N—H⋯O and C—H⋯O hydrogen bonds to form chains running along [101].

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 ▶); Cukurovali et al. (2006 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Lin & Sang (2009 ▶); Suleiman Gwaram et al. (2010 ▶); Li & Ban (2009 ▶); Lo & Ng (2009 ▶); Ning & Xu (2009 ▶); Zhu et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₂Cl₂N₂O₂
M _r = 323.17
Monoclinic,
a = 7.137 (1) Å
b = 28.146 (2) Å
c = 8.130 (1) Å
β = 115.098 (1)°
V = 1478.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.917, T _max = 0.928
8543 measured reflections
3211 independent reflections
2439 reflections with I > 2σ(I)
R _int = 0.080

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.130
S = 1.08
3211 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012419/ci5073sup1.cif

e-66-o1048-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012419/ci5073Isup2.hkl

e-66-o1048-Isup2.hkl^{(157.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.96	2.6689 (19)	144
N2—H2⋯O2ⁱ	0.90 (1)	2.13 (1)	2.9905 (19)	161 (2)
C7—H7⋯O2ⁱ	0.93	2.45	3.264 (2)	146

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Applied Chemistry Key Subject of Anhui Province (grant No. 200802187 C). The authors thank Mr Gang Wu of Chuzhou University for his help with the crystal growth.

supplementary crystallographic information

Comment

Hydrazone compounds have been widely investigated for their biological properties (Patil et al., 2010; Cukurovali et al., 2006). Furthermore, the crystal structures of the hydrazone compounds have also attracted much attention in recent years (Mohd Lair et al., 2009; Lin & Sang, 2009; Suleiman Gwaram et al., 2010). In the present work, the title new hydrazone compound is reported.

In the title molecule (Fig. 1), the dihedral angle between the two benzene rings is 6.3 (2)°. The molecule adopts an E configuration with respect to the C═N bond. There is an intramolecular O—H···O hydrogen bond (Table 1) in the molecule. All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable to those observed in related structures (Li & Ban, 2009; Lo & Ng, 2009; Ning & Xu, 2009; Zhu et al., 2009).

In the crystal structure, molecules are linked through intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) to form chains running along the [101] (Fig. 2).

Experimental

A mixture of 2,4-dichlorobenzaldehyde (0.174 g, 1 mmol) and 2-hydroxy-3-methylbenzohydrazide (0.166 g, 1 mmol) in methanol (50 ml) was stirred at room temperature for 1 h. The mixture was filtered to remove impurities, and then left at room temperature. After a few days, single crystals of the title compound, suitable for X-ray diffraction, were formed.